US5302657A - Highly dispersed organopolysiloxane emulsions - Google Patents
Highly dispersed organopolysiloxane emulsions Download PDFInfo
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- US5302657A US5302657A US07/891,901 US89190192A US5302657A US 5302657 A US5302657 A US 5302657A US 89190192 A US89190192 A US 89190192A US 5302657 A US5302657 A US 5302657A
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- polyorganosiloxane
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- emulsifier
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- mixture
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D19/00—Degasification of liquids
- B01D19/02—Foam dispersion or prevention
- B01D19/04—Foam dispersion or prevention by addition of chemical substances
- B01D19/0404—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance
- B01D19/0409—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance compounds containing Si-atoms
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
- D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2383/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
- C08J2383/04—Polysiloxanes
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/2962—Silane, silicone or siloxane in coating
Definitions
- the present invention relates to highly dispersed organopolysiloxane-containing emulsions and to a process for preparing highly dispersed organopolysiloxane-containing emulsions.
- emulsions are also described in WO 88/08 436 (laid-open on Nov. 3, 1988, H. Chrobaczek et al., Chemische Fabrik Pfersee GmbH). These emulsions are prepared from an aminoalkyl-substituted polyorganosiloxane, a water-soluble emulsifier, acid and water while heating to at least 50° C.
- steps (A) or (B) and more preferably steps (A) and (B), are carried out at temperatures below 50° C., and more preferably below 40° C.
- the organopolysiloxanes which are converted into a highly dispersed emulsion in the process of this invention contain, in particular, at least one ammonium-functional organopolysiloxane. At least 50 percent by weight, and in particular at least 75 percent by weight, of the organopolysiloxane preferably contain amino- and/or ammonium-functional organopolysiloxanes.
- the emulsions prepared by the process of this invention preferably have a mean particle size of less than 0.14 ⁇ m. These emulsions are transparent and generally clear.
- organopolysiloxanes of formula (I) are preferably employed:
- R represents the same or different hydrocarbon radicals having from 1 to 18 carbon atoms, substituted hydrocarbon radicals having from 1 to 18 carbon atoms, hydrocarbonoxy radicals having from 1 to 18 carbon atoms or substituted hydrocarbonoxy radicals having from 1 to 18 carbon atoms
- R' represents the same or different, Si-C-bonded substituted hydrocarbon radicals containing polar groups or hydroxyl groups
- n is an integer having a value of 0, 1, 2 or 3
- m is an integer having a value of 0, 1, 2 or 3
- the sum of n+m has an average value of from 1.8 to 2.2
- m has a value such that the organopolysiloxane contains at least one radical R'.
- radicals R may be replaced by hydrogen atoms bonded directly to silicon atoms; however, this is not preferred.
- the sum n+m preferably has an average value of from 1.9 to 2.1.
- R' is preferably an aminoalkyl or ammonium-alkyl radical.
- hydrocarbon radicals represented by R are alkyl radicals, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl and tert-pentyl radicals, hexyl radicals, such as the n-hexyl radical, heptyl radicals, such as the n-heptyl radical, octyl radicals, such as the n-octyl radical, and isooctyl radicals, such as the 2,2,4-trimethylpentyl radical, nonyl radicals, such as the n-nonyl radical, decyl radicals, such as the n-decyl radical, dodecyl radicals, such as the n-dodecyl radical, and octadecyl radicals, such as
- substituted hydrocarbon radicals represented by R are cyanoalkyl radicals, such as the ⁇ -cyanoethyl radical, and halogenated hydrocarbon radicals, for example haloalkyl radicals, such as the 3,3,3-trifluoro-n-propyl radical, the 2,2,2,2',2',2'-hexafluoroisopropyl radical and the heptafluoroisopropyl radical, and haloaryl radicals, such as the o-, m- and p-chlorophenyl radical.
- cyanoalkyl radicals such as the ⁇ -cyanoethyl radical
- halogenated hydrocarbon radicals for example haloalkyl radicals, such as the 3,3,3-trifluoro-n-propyl radical, the 2,2,2,2',2',2'-hexafluoroisopropyl radical and the heptafluoroisopropyl radical, and haloaryl radicals,
- hydrocarbonoxy and substituted hydrocarbonoxy radicals represented by R are substituted and unsubstituted hydrocarbon radicals R, mentioned in the above examples which are bonded via an oxygen atom to a silicon atom, and in particular alkoxy radicals having from 1 to 18 carbon atoms and phenoxy radicals, and more preferably the methoxy, ethoxy, n-propoxy, isopropoxy and phenoxy radicals.
- at most 5 percent of the radicals R are optionally substituted hydrocarbonoxy radicals.
- radicals R' are amino-functional hydrocarbon radicals, for example aminoalkyl radicals, such as the ⁇ -aminopropyl radical and the ⁇ -aminoethyl- ⁇ -aminopropyl radical; aminoaryl radicals; Si-C-bonded cyclic amino-functional radicals; ammonium-alkyl radicals, such as the radicals which can be formed from the above mentioned amino-functional hydrocarbon radicals by reaction with carboxylic or mineral acids or alkylating agents; hydroxyl groups, or carboxylic acid or sulphonic acid radicals which are bonded to the silicon atom via an alkylene or arylene group, or esters thereof; mercaptoalkyl radicals; and Si-C-bonded hydrocarbon radicals which contain epoxy, hydroxyl, amido and/or carboxyl groups,
- radicals represented by R' are amino-functional hydrocarbon radicals, for example aminoalkyl radical, such as the aminomethyl, 1- or 2-aminoethyl, 1-, 2- or 3-aminopropyl, 4-aminobutyl, N,N-dimethylaminomethyl and N-(2-aminoethyl)-3-aminopropyl radicals; aminoaryl radicals, such as o-, m, and p-aminophenyl radicals or o-, m- and p-(N,N-dimethylamino)-phenyl radicals; morpholine and piperidine radicals which are bonded to the silicon atom either directly or via an alkylene group; ammonium-functional hydrocarbon radicals which are obtained from the reaction of the amino-functional hydrocarbon radicals mentioned above with mineral acids, such as hydrochloric, perchloric, sulphuric, sulphurous, nitric, nitrous, hydrofluoric, phosphoric acid
- amido-functional radicals are the ⁇ -acetamidopropyl radical, and partially or fully acetylated ⁇ -aminoethyl- ⁇ -aminopropyl radicals,
- radicals represented by R' are the 3-aminopropyl radical, the N-(2-aminoethyl)-3-aminopropyl radical, and ammonium-functional radicals which can be prepared therefrom by reaction with the mineral and/or carboxylic acids mentioned above, and in particular with acetic acid.
- the radicals R are preferably methyl, ethyl, phenyl, methoxy and/or vinyl radicals. Due to their availability, 50 percent of the radicals represented by R, and more preferably at least 80 percent of the radicals R, are preferably methyl radicals.
- polyorganosiloxane preferably one of formula (I), or more than one polyorganosiloxane. If more than one polyorganosiloxane is employed, it is preferred that at least one polyorganosiloxane of formula (I) be employed. Specifically, it is possible to employ at least one polyorganosiloxane of formula (I) mixed with polydimethylsiloxanes containing terminal alkyl and/or alkoxy groups, each having from 1 to 4 carbon atoms, or only poly-organosiloxanes of formula (I). However, it is particularly preferred that only polyorganosiloxanes of formula (I) be employed, and more preferably one polyorganosiloxane of formula (I).
- the polyorganosiloxane (mixture) employed in the process of this invention is preferably liquid.
- the polyorganosiloxanes employed in the process of this invention each have viscosities of from 100 mPa.s to 1,000,000 mPa.s, in each case measured at 25° C.
- emulsifiers are required which are soluble in the polyorganosiloxane.
- the emulsifier employed in each case or the emulsifier mixture employed in each case must be soluble in the polyorganosiloxane.
- each emulsifier present therein is preferably soluble in the polyorganosiloxane.
- the solubility of an emulsifier or of an emulsifier mixture is preferably determined by mixing one part by weight of emulsifier or emulsifier mixture with one hundred parts by weight of polyorganosiloxane at 20° C. If the resultant mixture is clear, the emulsifier or emulsifier mixture is regarded as being soluble in the polyorganosiloxane.
- emulsifiers which may be employed in this invention include, in particular: Anionic emulsifiers:
- Alkyl sulphates particularly those having a chain length of from 8 to 18 carbon atoms, alkyl and alkyl ether sulphates having from 8 to 18 carbon atoms in the hydrophobic radical and from 1 to 40 ethylene oxide (EO) or propylene oxide (PO) units.
- EO ethylene oxide
- PO propylene oxide
- Sulphonates in particular alkylsulphonates having from 8 to 18 carbon atoms, alkylarylsulphonates having from 8 to 18 carbon atoms, taurides, esters and monoesters of sulphosuccinic acid with monohydric alcohols or alkylphenols having from 4 to 15 carbon atoms; if desired, these alcohols or alkylphenols may also be ethoxylated with from 1 to 40 EO units.
- Alkali metal and ammonium salts of carboxylic acids having from 8 to 20 carbon atoms in the alkyl, aryl, alkaryl or aralkyl radical.
- Partial esters of phosphoric acid, and alkali metal and ammonium salts thereof in particular alkyl and alkaryl phosphates having from 8 to 20 carbon atoms in the organic radical, alkyl ether phosphates and alkaryl ether phosphates having from 8 to 20 carbon atoms in the alkyl or alkaryl radical and from 1 to 40 EO units.
- Nonionic emulsifiers are nonionic emulsifiers:
- Alkyl polyglycol ethers preferably those having from 2 to 40 EO units and alkyl radicals having from 8 to 20 carbon atoms.
- Alkaryl polyglycol ethers preferably those having from 2 to 40 EO units and from 8 to 20 carbon atoms in the alkyl and aryl radicals.
- Ethylene oxide/propylene oxide (EO/PO) block copolymers preferably those having from 8 to 40 EO or PO units.
- Fatty acid polyglycol esters preferably those having from 6 to 24 carbon atoms and from 2 to 40 EO units.
- Natural products and derivatives thereof such as lecithin, lanolin, saponins, cellulose; cellulose alkyl ethers and carboxyalkylcelluloses whose alkyl groups each have up to 4 carbon atoms.
- Linear organopolysiloxane-containing polar groups in particular those containing alkoxy groups having up to 24 carbon atoms and/or up to 40 EO and/or PO groups.
- Quaternary alkyl- and alkylbenzeneammonium salts in particular those whose alkyl group has from 6 to 24 carbon atoms, preferably the halides, sulphates, phosphates and acetates.
- Alkylpyridinium, alkylimidazolinium and alkyloxazolinium salts in particular those whose alkyl chain has up to 18 carbon atoms, specifically the halides, sulphates, phosphates and acetates.
- emulsifiers can be employed in the process of this invention as long as they are soluble in the polyorganosiloxane.
- Preferred emulsifiers which are soluble in the polyorganosiloxane, are nonionic emulsifiers, in particular the nonionic emulsifiers listed above under 5. and 6., preferably the alkyl polyglycol ethers listed under 5., and more preferably alkyl polyglycol ethers having from 2 to 10 EO units and alkyl radicals of from 8 to 20 carbon atoms.
- the emulsions which can be prepared by the process of this invention preferably contain from 5 to 50 percent by weight, and more preferably from 10 to 25 percent by weight, of polyorganosiloxane, based on the sum of the weights of the polyorganosiloxane, the emulsifier and water.
- the emulsions which can be prepared by the process of this invention preferably contain the emulsifier in amounts of from 10 to 70 percent by weight, and more preferably from 20 to 40 percent by weight, based on the weight of the polyorganosiloxane employed.
- the emulsions of this invention may also contain additives. These are, in particular, bactericides, fungicides, algicides, microbicides, fragrances, corrosion inhibitors, dyes, pigments, thickeners, fillers and, although not preferred, organic solvents.
- the emulsions which can be prepared in accordance with this invention preferably contain additives in amounts of from 0 to 1 percent by weight, and more preferably from 0.01 to 0.1 percent by weight, based on the sum of the weights of the polyorganosiloxane, the emulsifier and water.
- step (A) of the process of this invention a concentrate is prepared from the polyorganosiloxane, the emulsifier which is soluble in the polyorganosiloxane, and water.
- these components can be added in any desired sequence, but it is preferred to first prepare a organosiloxane to this mixture.
- the amount of water added in step (A) is preferably from 5 to 100 parts by weight, and more preferably from 10 to 40 parts by weight, based on 100 parts by weight of the polyorganosiloxane.
- step (B) of the process of this invention is preferably effected by stepwise incorporation into the concentrate.
- step (A) or step (B) Warming of the mixture is not necessary either in step (A) or in step (B).
- the temperature in at least step (A) or step (B), or in both steps is preferably from 5° C. to 45° C., and more preferably from 10° C. to 40° C.
- the pressure exerted on the respective components or mixtures in step (A) is preferably the external pressure, if desired increased by mixing elements, of from 0.01 to 1 MPa (abs.), and more preferably from 0.09 to 0.11 MPa (abs.)
- ammonium-functional polyorganosiloxane preferably present in the emulsions of this invention and employed in the process of this invention can be prepared by adding mineral acids or carboxylic acids to appropriate amino-functional polyorganosiloxanes. It is preferred that the acid be added to the polyorganosiloxane before the polyorganosiloxane is employed in step (A) of the process of this invention. However, the reaction of the amino-functional polyorganosiloxanes may alternatively be carried out during step (A) by employing an appropriate amount of acid and amino-functional polyorganosiloxane in step (A). In both cases, it is preferred that the amount of acid be such that not all the amino groups of the amino-functional polyorganosiloxane be converted into ammonium groups.
- an amino-functional polyorganosiloxane is used to prepare the ammonium-functional siloxane preferably employed in the process of this invention, it is preferred that it has an amine number of from 0.1 to 3.0 and more preferably from 0.2 to 0.9.
- the amine number of an amino-functional substance is determined by the consumption in cm 3 of N hydrochloric acid on titration of 1 g of the amino-functional substance.
- the emulsion is preferably adjusted to a pH of from 3 to 7, and more preferably from 4 to 6, after step (B) by the addition of an acid.
- the pressure exerted on the concentrate during its dilution with water in step (B) is preferably the external pressure, if desired increased by mixing elements, of from 0.01 to 1 MPa (abs.), and more preferably from 0.09 to 0.11 MPa (abs.).
- the process of this invention may be carried out in any turbulent mixer which has been used heretofore or could have been used heretofore in the preparation of emulsions. As described heretofore, the mixer need not be capable of being heated.
- mixers which can be used in step (A) and step (B) are stirrers, such as paddle, straight-arm paddle, anchor, gate, screw, propeller, disc, impeller, turbine and planetary stirrers, single- and twin-screw mixers, mixing turbines, colloid mills, ultrasound mixers, in-line mixers, pumps, and homogenizers, such as high-pressure, turbine and circulating homogenizers.
- stirrers such as paddle, straight-arm paddle, anchor, gate, screw, propeller, disc, impeller, turbine and planetary stirrers, single- and twin-screw mixers, mixing turbines, colloid mills, ultrasound mixers, in-line mixers, pumps, and homogenizers, such as high-pressure, turbine and circulating homogenizers.
- the process of this invention can be carried out batchwise, continuously or semicontinuously.
- the process is preferably carried out continuously.
- the emulsions of this invention may be employed in all cases where silicone emulsions have been employed heretofore. They are particularly suitable for impregnating fibres and fabrics, in detergents and polishes, in paints or as impregnants for building materials and precursors thereof, in anti-foam agents and for coatings which repel tacky substances.
- textile fibres such as, for example as filament lubricants and textile fabrics
- cosmetics such as hand creams, body lotions, shampoos, hair rinses, hair setting lotions, shaving creams and lotions
- polishes such as furniture, floor and car polishes
- waxes such as floor waxes
- disinfectants for waterproofing gypsum before or after shaping to form building components
- emulsion paints in particular in silicone paints, in or as paper coatings for backings for self-adhesive labels, and as mould-release agents for polymers.
- a particularly preferred use of the emulsions of this invention is as agents or in agents for impregnating and coating textile fibres and fabrics.
- Polymer A Polydiorganosiloxane comprising dimethylsiloxy, methyl( ⁇ -aminoethyl- ⁇ -aminopropyl)-siloxy units and terminal trimethylsilyl groups; viscosity: 1,000 mPa.s at 25° C.; amine number: 0.6.
- Polymer B Polydiorganosiloxane comprising dimethylsiloxy, methyl( ⁇ -aminoethyl- ⁇ -aminopropyl)-siloxy units and terminal methoxydimethylsilyl groups; viscosity: 1,000 mPa.s at 25° C.; amine number: 0.3.
- Emulsifier C Isotridecyl alcohol polyglycol ether having 6 ethyleneoxy units, commercially available under the tradename Genapol® X060 from Hoechst AG, D-6000 Frankfurt/Main 80.
- An ammonium-functional polyorganosiloxane was prepared by mixing 170 parts by weight of polymer A with 3 parts of weight of 99.8 percent by weight of acetic acid.
- the emulsifier C is soluble in the resultant polymer.
- a concentrate was prepared by emulsifying 173 parts by weight of the polymer prepared in (a) above, 60 parts by weight of emulsifier C and 50 percent by weight of water.
- the maximum temperature achieved during the procedure described in Example 1 was 33° C.
- An ammonium-functional polyorganosiloxane was prepared by mixing 170 parts by weight of polymer B with 3 parts by weight of 99.8 percent by weight of acetic acid.
- the emulsifier C is soluble in the resultant polymer.
- a concentrate was prepared by emulsifying 173 parts by weight of the polymer prepared in (a) above, 60 parts by weight of emulsifier C and 50 percent by weight of water.
- the maximum temperature achieved during the procedure described in Example 2 was 33° C.
- the resultant pasty mixture was diluted very slowly and, as soon as the viscosity of the mixture had decreased, the water was added rapidly until a total of 637 parts by weight of water had been added, and then 0.5 parts by weight of a bactericidal, algicidal and corrosion-inhibiting additive were added.
- the pH of the resultant emulsion was subsequently adjusted to a value of 5.5 using dilute acetic acid.
- a water-clear emulsion having an average particle diameter of 25 nm was obtained.
- the maximum temperature achieved during the procedure described in Example 3 was 30° C.
- Examples 1, 2 and 3 were repeated in a continuous process, in which the concentrate prepared in a first mixer was diluted in a second mixer and further diluted in a second mixer with the appropriate amount of water and, if desired, an additive was added. In each case, water-clear emulsions having an average particle diameter of less than 100 nm were obtained. The maximum temperature achieved in each of these examples was 30° C.
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Abstract
Description
R.sub.n R'.sub.m SiO.sub.( 4-n-m)/2 (I)
Claims (10)
R.sub.n R'.sub.m SiO.sub.(4-n-m)/2 (I)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/891,901 US5302657A (en) | 1990-02-16 | 1992-06-01 | Highly dispersed organopolysiloxane emulsions |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4004946 | 1990-02-16 | ||
DE4004946A DE4004946A1 (en) | 1990-02-16 | 1990-02-16 | FINE-PART ORGANOPOLYSILOXANE EMULSIONS |
US66147991A | 1991-02-14 | 1991-02-14 | |
US07/891,901 US5302657A (en) | 1990-02-16 | 1992-06-01 | Highly dispersed organopolysiloxane emulsions |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US66147991A Continuation | 1990-02-16 | 1991-02-14 |
Publications (1)
Publication Number | Publication Date |
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US5302657A true US5302657A (en) | 1994-04-12 |
Family
ID=6400361
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US07/891,901 Expired - Fee Related US5302657A (en) | 1990-02-16 | 1992-06-01 | Highly dispersed organopolysiloxane emulsions |
Country Status (10)
Country | Link |
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US (1) | US5302657A (en) |
EP (1) | EP0442098B1 (en) |
JP (1) | JPH04363329A (en) |
KR (1) | KR950006158B1 (en) |
AT (1) | ATE138960T1 (en) |
AU (1) | AU631967B2 (en) |
BR (1) | BR9100271A (en) |
CA (1) | CA2035178C (en) |
DE (2) | DE4004946A1 (en) |
ES (1) | ES2087117T3 (en) |
Cited By (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5391400A (en) * | 1992-12-16 | 1995-02-21 | Osi Specialties, Inc. | Aqueous emulsion containing an oxidatively crosslinked aminopolysiloxane |
EP0692567A1 (en) | 1994-07-14 | 1996-01-17 | Wacker-Chemie GmbH | Amionofunctional organopolysiloxane |
US5503755A (en) * | 1992-09-26 | 1996-04-02 | Clariant Finance (Bvi)Limited | Aqueous wax and silicone dispersions, their production and use |
US5578298A (en) * | 1994-05-27 | 1996-11-26 | General Electric Company | Microemulsions for high viscosity amino silicone fluids and gums and their preparation |
US5593611A (en) * | 1992-06-29 | 1997-01-14 | Osi Specialties, Inc. | Method for imparting softness with reduced yellowing to a textile using a low amine content, high molecular weight aminopolysiloxane |
US5593483A (en) * | 1995-03-27 | 1997-01-14 | Advanced Chemical Technologies, Inc. | Water repellent composition for cellulose containing materials and method for producing same |
US5627148A (en) * | 1991-07-04 | 1997-05-06 | Oreal | Washing and/or conditioning composition for keratinous materials based on a silicone containing a hydroxyacylamino functional group and on substantive polymers |
US5683625A (en) * | 1994-05-27 | 1997-11-04 | General Electric Company | Method of preparing microemulsions |
US5712343A (en) * | 1993-08-27 | 1998-01-27 | Wacker-Chemie Gmbh | Preparation of organopolysiloxane microemulsions |
US6008145A (en) * | 1996-11-04 | 1999-12-28 | Schill & Seilacher Gmbh & Co. | Composition for the permanent hydrophilation of polyolefin fibres, use of the composition and fibres treated therewith |
US6054020A (en) * | 1998-01-23 | 2000-04-25 | Kimberly-Clark Worldwide, Inc. | Soft absorbent tissue products having delayed moisture penetration |
US6093410A (en) * | 1997-11-05 | 2000-07-25 | The Procter & Gamble Company | Personal care compositions |
US6207720B1 (en) * | 1999-06-25 | 2001-03-27 | Crompton Corporation | Hydrolyzable silane emulsions and method for preparing the same |
SG83806A1 (en) * | 1999-12-30 | 2001-10-16 | Shih Ying Chi | A long-acting disinfectant and its preparation method |
US6572968B2 (en) * | 1995-06-27 | 2003-06-03 | Hitachi Chemical Co., Ltd. | Method of producing prepreg for printed wiring boards, glass fiber material treated with silicone oligomer, and laminate for printed wiring boards |
US6649692B2 (en) | 2001-02-20 | 2003-11-18 | Crompton Corporation | Organopolysiloxane composition, emulsion-forming concentrates and aqueous emulsions formed therefrom and use of the emulsions in the treatment of textiles |
US20040198842A1 (en) * | 2003-04-03 | 2004-10-07 | Marcus Bocker | Aqueous defoamer formulations |
US20050282914A1 (en) * | 2004-06-18 | 2005-12-22 | Reed Ted A | Continuous manufacture of high internal phase ratio emulsions using relatively low-shear and low-temperature processing steps |
EP1975193A1 (en) | 2007-03-28 | 2008-10-01 | CHT R. BEITLICH GmbH | Polysiloxane and textile aid containing a polysiloxane |
US20100256244A1 (en) * | 2009-04-03 | 2010-10-07 | Kroff Chemical Company | Demulsification Compositions, Systems and Methods for Demulsifying and Separating Aqueous Emulsions |
WO2011042409A2 (en) | 2009-10-05 | 2011-04-14 | Momentive Performance Materials Gmbh | Aqueous emulsions of polyorganosiloxanes |
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US5712343A (en) * | 1993-08-27 | 1998-01-27 | Wacker-Chemie Gmbh | Preparation of organopolysiloxane microemulsions |
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US6093410A (en) * | 1997-11-05 | 2000-07-25 | The Procter & Gamble Company | Personal care compositions |
US6054020A (en) * | 1998-01-23 | 2000-04-25 | Kimberly-Clark Worldwide, Inc. | Soft absorbent tissue products having delayed moisture penetration |
US6207720B1 (en) * | 1999-06-25 | 2001-03-27 | Crompton Corporation | Hydrolyzable silane emulsions and method for preparing the same |
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US6649692B2 (en) | 2001-02-20 | 2003-11-18 | Crompton Corporation | Organopolysiloxane composition, emulsion-forming concentrates and aqueous emulsions formed therefrom and use of the emulsions in the treatment of textiles |
US20040198842A1 (en) * | 2003-04-03 | 2004-10-07 | Marcus Bocker | Aqueous defoamer formulations |
US20050282914A1 (en) * | 2004-06-18 | 2005-12-22 | Reed Ted A | Continuous manufacture of high internal phase ratio emulsions using relatively low-shear and low-temperature processing steps |
US7144148B2 (en) * | 2004-06-18 | 2006-12-05 | General Electric Company | Continuous manufacture of high internal phase ratio emulsions using relatively low-shear and low-temperature processing steps |
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US20080261473A1 (en) * | 2007-03-28 | 2008-10-23 | Peter Will | Polysiloxane and textile auxilary containing a polysiloxane |
US20110097567A1 (en) * | 2008-06-13 | 2011-04-28 | Clariant Finance (Bvi) Limited | Polydiorganosiloxane Bearing Carbamate Functions, Their Preparation And Their Use As Softeners In The Textile Industry |
US20110104085A1 (en) * | 2008-06-13 | 2011-05-05 | Clariant Finance (Bvi) Limited | Cosmetic Or Pharmaceutical Compositions Comprising Modified Polysiloxanes With At Least One Carbamate Group |
US8815755B2 (en) | 2008-06-13 | 2014-08-26 | Clariant Finance (Bvi) Limited | Polydiorganosiloxane bearing carbamate functions, their preparation and their use as softeners in the textile industry |
US20100256244A1 (en) * | 2009-04-03 | 2010-10-07 | Kroff Chemical Company | Demulsification Compositions, Systems and Methods for Demulsifying and Separating Aqueous Emulsions |
US8268975B2 (en) | 2009-04-03 | 2012-09-18 | Dow Agrosciences Llc | Demulsification compositions, systems and methods for demulsifying and separating aqueous emulsions |
US8796433B2 (en) | 2009-04-03 | 2014-08-05 | Kroff Chemical Company | Demulsification compositions, systems and methods for demulsifying and separating aqueous emulsions |
US9308474B2 (en) | 2009-04-03 | 2016-04-12 | Kroff Chemical Company | Demulsification compositions, systems and methods for demulsifying and separating aqueous emulsions |
WO2011042409A2 (en) | 2009-10-05 | 2011-04-14 | Momentive Performance Materials Gmbh | Aqueous emulsions of polyorganosiloxanes |
US10773405B2 (en) * | 2016-06-30 | 2020-09-15 | The Gillette Company Llc | Shaving aid for razor cartridges comprising a nano-filament comprising a core and sheath |
CN108753159A (en) * | 2018-06-29 | 2018-11-06 | 无锡鸿孚硅业科技有限公司 | A kind of organic silicon emulsion concrete waterproofer and preparation method thereof |
Also Published As
Publication number | Publication date |
---|---|
CA2035178A1 (en) | 1991-08-17 |
EP0442098A2 (en) | 1991-08-21 |
ATE138960T1 (en) | 1996-06-15 |
KR910021447A (en) | 1991-12-20 |
AU631967B2 (en) | 1992-12-10 |
DE59010359D1 (en) | 1996-07-11 |
CA2035178C (en) | 1997-11-11 |
EP0442098B1 (en) | 1996-06-05 |
AU7106991A (en) | 1991-08-22 |
DE4004946A1 (en) | 1991-08-22 |
EP0442098A3 (en) | 1993-01-20 |
ES2087117T3 (en) | 1996-07-16 |
BR9100271A (en) | 1991-10-22 |
JPH04363329A (en) | 1992-12-16 |
KR950006158B1 (en) | 1995-06-09 |
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